Substituted 1,2,4-oxadiazolidine-3,5-dione

ABSTRACT

2-(3-TERT-BUTYLCARBAMOYLOXYPHENYL)-4-METHYL-1,2,4OXADIAZOLIDINE-3,5-DIONE WHICH HAS A GOOD HERBICIDAL ACTION AND A PROCESS FOR CONTROLLING THE GROWTH OF UNWANTED PLANTS WITH THIS COMPOUND.

D United States Patent H 1 9 a 1 5 Zschocke et al. 51 Oct. 3, 1972 [54]SUBSTITUTED 1,2,4- [58] Held 0! Search ..260/307 8OXADlAZOLlDINE-3,5-DIONE 721 Inventors: Albrecht mm, s Berliner [56]Strasse, 6702 Bad Duerkheim; FOREIGN PATENTS OR APPLICATIONS Bemd Zach,3 Thorwaldsenstrasse, 6700 Ludwigshafen; Adolf Escher, "560ml 3/1969 43Speyerer Strasse, 6704 Mut- Primary m Maze] terstadt of GermanyAssistant Examiner-11. V. Rush 22 Filed; Oct 7, 1979 Anonwy-Johnston,Root, O'Keeffe, Keil, Thompson & Shurtleff [21] Appl. No: 78,974

[57] ABSTRACT [30] Foreign Application Priority Data 2-(3-tert-butylcarbamoyloxyphenyl)-4-methyl-l,2,4-

oxadiazolidine-3,5-dionc which has a good herbicidal Germany 19 8800action and a process for controlling the growth of unht d. [52] us. Cl...260/307 B, 71/92 want [51 Int. Cl. ..C07cl 85/52 1 Claim, No DrawingsSUBSTITUTED 1,2,4-XADlAmLlDlNE-3,5-

DiONE it is known to use 2-(B-dimethylcarbamoyloxyphenyl)-4-methyl-l,2,4-oxadiazo1idine-3,S-dione as a herbicide (Belgian Pat. No. 714,355;French Pat. No. 1,560,971); however, its action is not satisfactorybecause unwanted plants are not injured to a sufficient extent.

We have now found that 2-( S-tert-butylcarbamoyloxyphenyl )-4-methyl- 1,2,4-oxadiazolidine-3,5- dione of the formula has a good herbicidalaction.

The production of the compound of the invention is described below;parts in the examples are by weight.

EXAMPLE I 41.7 parts of 3-nitrophenol and 6.5 parts of ammonium chlorideare suspended or dissolved in 75 parts of water and 150 parts ofethanol; at a temperature of 70 to 80 C and in a nitrogen atmosphere, 52parts of zinc dust is introduced in portions into the suspension whilestirring well. The mixture is then filtered and the residue washed with150 parts of alcohol. At a temperature of 20 to 30 C, in a nitrogenatmosphere and while stirring well, 45.5 parts of methyl N-methyl-N-chloroformylcarbamate is added to the filtrate. The precipitate issuction filtered, washed with diluted alcohol and dried. 52 parts of2-(3-hydroxyphenyD-4- methyl-l,2,4-oxadiazolidine-3,S-dione having amelting point of 175 C is obtained.

EXAMPLE 2 20.8 parts of 2-(3-hydroxyphenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione is suspended in 50 parts of dioxane to which 3drops of triethylamine have been added; 99 parts of tert-butylisocyanate is introduced into the suspension. The mixture is kept for 2hours at 90 C and then cooled; the solvent is removed in vacuo and theresidue recrystallized from isopropanol. 22 parts of 2-(3-tert-butylcarbamoyloxyphenyl)-4-rnethyll,2,4-oxadiazolidine-3,5-dionehaving a melting point of 131C is obtained.

The herbicides according to the invention may be used as solutions,emulsions, suspensions or dusts. The form of application dependsentirely on the purpose for which the agents are being used; in any caseit should ensure a fine distribution of the active ingredient.

For the preparation of solutions to be sprayed direct, hydrocarbonshaving boiling points higher than 150C, e.g. tetrahydronaphthalene oralkylated napthalenes, or organic liquids having boiling points higherthan 150 C and having one or more than one functional group, eg the ketogroup, the ether group, the ester group or the amide group, this groupor these groups being attached as substituent(s) to a hydrocarbon chainor being a component of a heterocyclic ring, may be used as sprayliquids.

Aqueous formulations may be prepared from emulsion concentrates, pastesor wettable powders by adding water. To prepare emulsions theingredients as such or dissolved in a solvent may be homogenized inwater or organic solvents by means of wetting or dispersing agents, e.g.polyethylene oxide adducts. Concentrates which are suitable for dilutionwith water may be prepared from active ingredient, emulsifying ordispersing agent and possibly solvent.

Dusts may be prepared by mixing or grinding the active ingredients witha solid carrier, e.g. kieselguhr, talc, clay or fertilizers.

it is also possible to add insecticides, fungicides, bactericides andother herbicides to the herbicides according to the invention, or to mixthem with fertilizers. The application of the compound of the inventionis illustrated by the following example.

EXAMPLE 3 Outdoors, the plants Zea mays, Triticum vulgare, Sinapisarvensis, Galium aparine, Poa annua, Alopecurus myosuroides, Echinochloacrusgalli and Setaria glauca are treated at a growth height of 3 to l8cm with 1 kg per hectare of each of the following active ingredients,each amount being dispersed in 500 liters of water per hectare:

l. 2-( 3-tert-butylcarbamoyloxyphenyl)-4-methyll ,2,4-oxadiazolidine-3,5-dione;

II. 2-( 3-isopropylcarbamoyloxyphenyl)-4-methyll,2,4-oxadiazolidine-3,5-dione; Ill. 2-(3-dimethylcarbamoyloxyphenyl)-4-methyll ,2,4-oxadiazolidine-3,5-dione.After 2 to 3 weeks it is ascertained that compound I has a strongerherbicidal action than compounds 11 and ill. The results of theexperiment are given in the following table:

parts by weight of compound I is mixed with 30 parts by weight ofN-methyl-a-pyrrolidone. A mixture is obtained which is suitable forapplication in the form of very fine drops.

EXAMPLE 5 20 parts by weight of compound 1 is dissolved in a mixtureconsisting of parts by weight of xylene, 10 parts by weight of theadduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt ofdodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40moles of ethylene oxide to 1 mole of castor oil. By pouring the solutioninto 100,000

parts by weight of water and uniformly distributing it therein, anaqueous dispersion is obtained containing 0.02 percent by weight of theactive ingredient.

EXAMPLE 6 EXAMPLE 7 parts by weight of compound I is dissolved in amixture consisting of parts by weight of cyclohexanol, 65 parts byweight of a mineral oil fraction having a boiling point between 210 and280 C, and 10 parts by weight of the adduct of 40 moles of ethyleneoxide to 1 mole of castor oil. By pouring the solution into 100,000parts by weight of water and uniformly distributing it therein, anaqueous dispersion is obtained containing 0.02 percent by weight of theactive ingredient.

EXAMPLE 8 20 parts by weight of compound 1 is well mixed with 3 parts byweight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 17parts by weight of the sodium salt of a lignin-sulfonic acid obtainedfrom a sulfite waste liquor, and 60 parts by weight of powdered silicagel, and triturated in a hammer mill. By uniformly distributing themixture in 20,000 parts by weight of water, a spray liquid is obtainedcontaining 0.1 percent by weight of the active ingredient.

EXAMPLE 9 3 parts by weight of compound 1 is intimately mixed with 97parts by weight of particulate kaolin. A dust is obtained containing 3percent by weight of the active ingredient.

EXAMPLE [0 30 parts by weight of compound 1 is intimately mixed with amixture consisting of 92 parts by weight of powdered silica gel and 8parts by weight of paraffin oil which has been sprayed onto the surfaceof this silica gel. A formulation of the active ingredient is obtainedhaving good adherence.

We claim:

1. 2-( 3-tert-butylcarbamoyloxyphenyl )-4-methy1-l,2,4-oxadiazolidine-3,S-dione of the formula 21%? UNITED STATESPA'IICNT OFFICE CERTIFICATE OF CORRECTION Patent No. 5 9 5 Dated October3, 1972 e. 1; Inventor) Zechome Cu 211 It is certified that errorappears in the above-identified patent and that said Letters Patent arehereby corrected as shown below:

rm- Cover page, left hand column, insert {75] ASSIGNEE: Badische Anilin-& Soda- Fabrik. Aktiengesellschaft Ludwigshafen am Rhein, GermanySigned and sealed this 17th day of April 1973.

(SEAT) Attest:

